The narrative is now presented in a form of dramatic writing: in dialogue form with stage directions. Rosalind Connage, Alec's sister, is coming out (an occasion marking a girl's entry into debutante society) at the Connage house in New York, and Amory is present. We learn from stage directions and from her mother, sister, and brother's comments as Rosalind prepares that Rosalind is a beautiful, sophisticated, somewhat spoiled and self-involved girl. Amory accidentally enters her dressing room and the two converse like professional socialites--a conversation that has rules. They kiss after several minutes. Rosalind boasts that she was expelled from Spence, her school, and that she has kissed dozens of men and will probably kiss dozens more. Amory distinguishes between a sentimental person, who thinks that things will last, and a romantic person, who hopes that they won't. He leaves wanting to kiss her again but Rosalind refuses, saying that she has won their exchange.
Rosalind's mother reappears, explaining to her daughter the ways to lure a wealthy a man, like Dawson Ryder, and urges her to follow the rules. Several hours later Rosalind dismisses a former beau, meets Dawson, and then falls in love with Amory. The novel shifts back to traditional narration and describes how the two spend several intense months being completely in love. Amory takes a job at an advertising agency in an attempt to make enough money to satisfy Rosalind.
The novel shifts back to dialogue form as Rosalind's mother complains that Rosalind is spending too much time with Amory and not with a wealthier man. Amory appears looking quite haggard and Rosalind, painfully and reluctantly, breaks off their engagement, saying she needs to be with a wealthy man and would not be the woman that Amory loved for long if they were to live without money. Amory is finally forced to leave in defeat.
Amory does not find much peace upon his return from the war, instead finding himself involved in an intense romance. This first scene contains not only the imaginative stylistic innovations of the young Fitzgerald, including different narrative forms and a shocking portrayal of a young debutante, but also the most important romance of the novel. Fitzgerald's decision to switch to dialogue form beautifully captures the intensity of Amory and Rosalind's interchanges in a way prose could not.
The portrait of Rosalind, especially her line about how many men she both has kissed and plans to kiss, is refreshingly feminist for its time. Her mother's platitudes convey the ways in which a young debutante was supposed to operate, but Rosalind glibly oversteps her bounds in every way in search of fun and some semblance of sexual liberation. This scene, with its honest depiction of the attitudes of the young elite, was crucial to establishing Paradise as the popular success it became.
Amory, for the first time, is not assuming some pose. He falls head over heels in love with Rosalind and is quite beyond his own control, surprising even himself. The love they share constitutes one of the most intense experiences Amory has ever had, and Amory agrees to conventionalize himself for the sake of it, taking the advertising job in the hopes of marrying Rosalind.
But money plays too important a role in their lives for the young girl to give up a wealthy lifestyle. With extraordinary psychological insight, no doubt gleaned from his own experiences, Fitzgerald explores the impact that lack of money would have on the relationship, concluding that Rosalind would cease to be the woman that Amory loved if subjected to life without resources. Rosalind's decision to break off their engagement functions as the most devastating experience for Amory, the one that fuels his decisions for the remainder of the book. He will never love again as he loved Rosalind, and he is shattered by her decision.